TW200918640A - Organic electroluminescence device - Google Patents

Abstract

Disclosed is an organic electroluminescent device which comprises an organic thin film composed of one or more layers between a cathode and an anode. The organic thin film contains at least one light-emitting layer, and at least one of the light-emitting layers contains at least one phosphorescent material and a host material represented by the following formula (1). (In the formula, Ar1, Ar2, Ar3, B1, B2, B3 and B4 respectively represent a substituted or unsubstituted benzene ring or a fused aromatic hydrocarbon ring selected from a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring and a substituted or unsubstituted triphenylene ring; and p represents 0 or 1.)

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device (hereinafter sometimes referred to simply as an organic EL device). In particular, it relates to a light-emitting layer that emits green light. [Prior Art] It is known that an organic thin film layer containing a light-emitting layer is provided between an anode and a cathode, and an organic electroluminescence obtained by recombination of a hole injected into a light-emitting layer and electrons to obtain an illuminating organic electroluminescence element. The organic electroluminescence device can be used as a self-luminous device, and it is expected to be a light-emitting device which is excellent in luminous efficiency, image quality, power consumption, and thin design. Further improvement of the organic electroluminescence device is, for example, luminous efficiency. In this regard, in order to improve the internal quantum efficiency, the development of a luminescent material (twilight luminescent material) obtained from the luminescence of a triplet agonist has recently been reported as a luminescent light-emitting organic electroluminescent device. The use of such a luminescent material to form a light-emitting layer (a light-emitting layer) can achieve an internal quantum efficiency of 75% or more, theoretically close to 1%, and a high-efficiency organic light-emitting element with low power consumption. Further, in order to form a light-emitting layer, a doping method in which a host material is blended into a blend of a light-emitting material is known. In the light-emitting layer formed by the doping method, an agonist can be efficiently generated by the charge injected into the host material. The agonist energy of the generated agonist -5-200918640 is moved to the blend, and the self-blend can obtain high-efficiency luminescence. Among them, in order to carry out intermolecular energy transfer of the autonomous material in the luminescent luminescent luminescent mixture, the excited triplet energy EgH of the main material must be larger than the stimulating triplet energy EgD of the luminescent mixture. CBP (4,4 ' _bis(N-carbazolyl)biphenyl) is known as a material which is a much effective material for activating the triplet energy (for example, reference 1: US2002/182441) . When the CBP is used as a main material, energy transfer for a calendering blend showing a predetermined luminescent wavelength (e.g., green, red) can be performed, and a highly efficient organic electroluminescent device can be obtained. However, when CBP is used as a main material, the luminous efficiency by the luminescent light can be particularly improved, but on the other hand, the life is very short and it is not practical. This is presumed to be that the oxidation stability of the molecular structure of CBP is not high, and the molecular deterioration of the hole is intense. Further, in the literature 2 (WO 2005/112519), a condensed ring derivative containing a nitrogen-containing ring such as carbazole is used as a main material for displaying a neon light-emitting light-emitting layer. With this technique, the luminous efficiency and the lifetime can be improved, but they are not sufficiently put into practical use. On the other hand, it is known that various kinds of fluorescent materials for fluorescent blends (fluorescent main materials) and fluorescent dye blends have been reported to form fluorescent light with excellent luminous efficiency and longevity. The main material of the luminescent layer. However, in the 'fluorescent main material', the 1st energy Eg (S) is larger than the fluorescent blend, but the triplet energy eg (T) is not large, so it cannot be used as a light. The main material of the luminescent layer (the luminescent main material) is used. For example, an anthracene derivative is known as a fluorescent main material. However, the stimulating triplet energy Eg (T) of the anthracene derivative is smaller than the degree of 1.9 eV. Therefore, a phosphor blend having a light-emitting wavelength of a visible light region of 480 nm to 550 nm cannot ensure its energy shift. Further, the excited triplet energy cannot be enclosed in the light-emitting layer. Therefore, anthracene derivatives are not suitable for use as a calender master material. Further, an anthracene derivative, an anthracene derivative, and a derivative of a butyl group are not suitable as a calender master material for the same reason. Further, an example in which an aromatic hydrocarbon compound is used as a calendering main material is known (Document 3: JP-A-200 3 - 1 42267). Among them, a compound in which two aromatic groups are bonded at a meta position as a substituent by using a benzene skeleton as a substituent is used as a calender master material. However, since the aromatic hydrocarbon compound of Document 3 has a molecular structure in which the central benzene skeleton is a symmetrical under-molecular extension molecule, there is a problem that the luminescent layer is easily crystallized. One, Document 4 (WO 2007/0 46658), Document 5 (Japanese Unexamined Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. An organic electroluminescence device using various aromatic hydrocarbon compounds is disclosed in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. 2005-75. However, there is no mention of the effectiveness as the main material of the enamel. As mentioned above, the energy can be efficiently moved in the luminescent material, and the main material of the practical length of 200918640 is unknown, and the components of the material are put into practical use. Obstructed. Among them, an object of the present invention is to provide an organic electroluminescent device which is highly efficient in luminescence. SUMMARY OF THE INVENTION The present inventors have made it possible to achieve the above object in detail by using a host material represented by the following formula (1) as a light-emitting organic light having a high efficiency and a long lifetime. The organic electroluminescence device of the present invention is an organic thin film layer formed by a cathode and a layer or a plurality of layers, wherein at least one of the organic light-emitting layers 'the light-emitting layer contains a main material and at least one kind of light that exhibits a neon light emission 〇

Ra-Ar'-Ar2-Ar3-Rb (1) In the above formula (1), a substituted or unsubstituted benzene ring, or a substituted or unsubstituted substituted tribenzophenone ring of Ra, Rb, Ar1, Ar2 and A substituted or unsubstituted phenanthrene ring.

When Ar2 is a substituted or unsubstituted benzene ring or a substituted phenanthrenyl or tribenzobenzene ring, [Ra_Arl_] and a group having a different structure. The result of using the luminescence luminescence rate and the long-life luminescence recovery method can be obtained by using a material, and the film layer having at least 1 between the anodes and the luminescent material represented by the formula (1) is a characteristic 5: Ar3 2,7_[Rb-Ar3 -], which is selected from the group consisting of a naphthalene ring, a substituted or a non-condensed aromatic hydrocarbon, or an unsubstituted. The invention is based on the use of the main material shown in the above formula (n as a calendering main material). The present invention is described below with reference to an embodiment of the present invention. (Configuration of Organic Electroluminescence Element) First, the composition of an organic electroluminescence element is described. As a representative element of the organic electroluminescence element, (1) anode/light-emitting layer/cathode (2) anode/hole injection layer/light-emitting layer/cathode (3) anode/light-emitting layer/electron injection ·Transport layer/cathode (4) anode/hole injection layer/light-emitting layer/electron injection/transport layer/cathode (5) anode/organic semiconductor layer/light-emitting layer/cathode (6) anode/organic semiconductor layer/electronic barrier layer /Lighting layer / Pole (7) Anode / Organic Semiconductor Layer / Luminous Layer / Adhesion Improvement Layer / Cathode (8 ) Anode / Hole Injection / Transport Layer / Luminous Layer / Electron Injection / Transport Layer / Cathode (9) Anode / Insulation / Luminous Layer /Insulation/Cathode (10) Anode/Inorganic Semiconductor Layer/Insulation Layer/Light Emitting Layer/Insulation Layer/Cathode (11) Anode/Organic Semiconductor Layer/Insulation Layer/Light Emitting Layer/Insulation Layer/Yin-9- 200918640 Pole (12 Structure of anode/insulation layer/hole injection/transport layer/light-emitting layer/insulation layer/cathode (13) anode/insulation layer/hole injection/transport layer/light-emitting layer/electron injection/transport layer/cathode. The configuration of (8) is preferably used, but is not limited to the same. Fig. 1 shows an example of an organic electroluminescent device according to an embodiment of the present invention. The organic electroluminescent device 1 has a transparent substrate 2. The anode 3, the cathode 4, and the organic thin film layer 10 disposed between the anode 3 and the cathode 4. The organic thin film layer 10 has a calender emitting layer 5 containing a calendering main material and a calendering blend, but the calendering layer 5 and the anode There is a hole injection between the 3, the transport layer 6 and the like, and between the phosphorescent layer 5 and the cathode 4 An electron injecting/transporting layer 7 or the like may be provided. Further, an electron barrier layer may be provided on the anode 3 side of the phosphorescent layer 5, and a hole barrier layer may be provided on the cathode 4 side of the phosphorescent layer 5. The hole is enclosed in the luminescent layer 5, which increases the probability of generation of the agonist in the luminescent layer 5. And in the present specification, the terms of the fluorescent main material and the luminescent main material are combined with the fluorescent blend. It is called the fluorescent main material, and the δ-inch, which is called the luminescent main material, is not limited to the narrow fluorescent main material or the fluorescent main material by molecular structure. In other words, in the present specification, the fluorescent main material means a material constituting the fluorescent light-emitting layer containing the -10-200918640 camping conjugate, and it is not only the main material of the fluorescent material. The same luminescent main material means that the material constituting the luminescent layer containing the luminescent mixture does not mean that only the main material of the luminescent material can be utilized. In the present specification, "hole injection/transport layer" means "at least one of the hole injection layer and the hole transport layer", and "electron injection. transport layer" means "at least one of the electron injection layer and the electron transport layer". One party." (Translucent Substrate) The organic electroluminescence device is fabricated on a light-transmitting substrate. The light-transmitting substrate is preferably a substrate supporting an organic electroluminescence device, and a smooth substrate having a light transmittance of 50% or more in a visible light region of 400 to 700 nm is preferable. Specifically, a glass plate, a polymer plate, etc. are mentioned. Specific examples of the glass plate include soda lime glass, barium saw glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz. Further, examples of the polymer sheet include polycarbonate, acryl, polyethylene terephthalate, polyether sulfide, and polyfluorene. (Anode and cathode) The anode of the organic electroluminescence device is effective when the role of injecting a hole into the hole injection layer, the hole transport layer or the light-emitting layer has a work function of 4_5 eV or more. Specific examples of the anode material include indium tin oxide alloy (-11 - 200918640 IΤ Ο ), tin oxide (Ν Ε S A ), indium oxide lead oxide, gold, silver, uranium, copper, and the like. The anode can be produced by forming a thin film of the electrode material by a vapor deposition method or a sputtering method. In the present embodiment, when the light emission from the light-emitting layer is taken out from the anode, it is preferable to make the light transmittance of the visible light region of the anode larger than 10%. Further, the sheet resistance of the anode is preferably several hundred Ω / □ or less. The film thickness of the anode is generally selected from the range of 10 nm to 1/zm, preferably 10 to 200 nm, depending on the material. As the cathode, for the purpose of injecting electrons into the electron injecting layer, the electron transporting layer or the light emitting layer, a material having a small work function is preferable. The cathode material is not particularly limited, and specifically, indium, indium, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-niobium-lithium alloy, magnesium-silver alloy, or the like can be used. Similarly to the anode, the cathode can be produced by forming a thin film by a vapor deposition method or a sputtering method. Further, it is also possible to take out the form of light emission from the cathode side. (Light Emitting Layer) The light emitting layer of the organic electroluminescence element has the following functions. That is, (1) the injection function; when the electric field is applied, the anode or the hole injection layer can be injected into the hole, and the function of the electron can be injected by the cathode or the electron injection layer' (2) the transport function; the injected charge (electron) And the hole) the function of moving the electric field force by -12-200918640, (3) the illuminating function; providing the recombination place of the electron and the hole, and the function related to the illuminating. However, the ease of injection of the hole and the ease of electron injection may have a difference, and the transport energy of the hole and the mobility of the electron may also differ. As a method of forming the light-emitting layer, for example, a known method such as a vapor deposition method, a spin coating method, or an LB method can be applied. The light-emitting layer is preferably a molecular deposition film. The molecular deposition film is a film formed by precipitation of a material compound in a gas phase state, or a film formed by solidification of a material compound in a solution state or a liquid phase state. Generally, the molecular deposition film can be obtained by the LB method. The formed film (molecular accumulation film) is distinguished by a difference in agglomerated structure, high-order structure, or functional difference caused by it. In the case where a binder such as a resin and a material compound are dissolved in a solvent to form a solution, the film can be formed into a light by a spin coating method or the like, as disclosed in Japanese Laid-Open Patent Publication No. Hei 57-51781. Floor. Further, the film thickness of the light-emitting layer is preferably from 5 to 50 nm, more preferably from 7 to 50 nm', most preferably from 10 to 5 nm. When it is less than 5 nm, it is difficult to form a light-emitting layer, and it is difficult to adjust the chromaticity. When the voltage exceeds 50 nm, the driving voltage may rise. In the present invention, the light-emitting layer contains at least one type of luminescent material that exhibits luminescence, and the following formula (1) the main material shown;

Ra-Ar1 -Ar2-Ar3-Rb ·· (1 ) -13- 200918640 In the above formula (1), 'Ra, Rb, Ar1, Ar2 and Ar3 in the formula (1) represent a benzene ring selected from substituted or unsubstituted benzene rings. Or a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted tribenzobenzene ring, and a substituted or unsubstituted phenanthrene ring condensed aromatic hydrocarbon ring. When A r 2 is a substituted or unsubstituted benzene ring, or a substituted or unsubstituted 2,7-phenanthryl or tribenzophenyl group, [Ra-Ar1-] and [Rb_Ar3-] have mutually different structures. base. Since the main material of the above formula (1) has a large triplet energy gap (excited triplet energy), the amount of the calendered blend may be shifted to cause luminescence. Further, an anthracene derivative known as a fluorescent main material is unsuitable as a main material for a red-emitting luminescent mixture, but the main material of the present invention has a large triplet energy gap, so that the display can be effectively emitted. A green light calender blend illuminates. However, in the CBP of the conventionally known light-emitting main material, a light-emitting blend having a shorter wavelength than green can also function as a main material, and in the main material of the present invention, only the green light-emitting light-emitting blend can be exhibited. Further, in the present invention, when the skeleton of the main material contains a polycyclic condensed ring having no nitrogen atom as a partial structure, the stability of the molecule can be improved and the life of the device can be prolonged. At this time, when the number of nuclear carbons in the skeleton portion is too small, the molecular stability cannot be sufficiently improved. On the other hand, when the number of the condensed rings of the polycyclic condensed ring constituting the compound of the present invention is too large, the conjugate is excessively extended to narrow the HOMO-LUMO distance, and the useful light-emitting wavelength of the triplet energy gap cannot be satisfied. In this regard, the main material of the formula (1) of the formula (1) has a moderate number of nuclear atoms, and therefore can be used as a calendering main material of a neon light-emitting layer having an excellent light-emitting wavelength and high stability. In the past, the wide-wavelength region selected from green to red corresponds to the main material widely used for the calendering blend of the calendering blend. Therefore, C B P having a wide triple-gap energy gap is used as the main material. However, the triplet energy gap Eg ( τ ) in 'CBP is indeed wider, but it has a shorter life. This point 'in the present invention' is not applicable to the main material of the calendering blend for obtaining a wide gap of blue light, and the function of the calendering blend for red light or green light can be used as a main material. . Moreover, if the CBP-like double-state energy gap is too wide, the main material of the present invention is suitable for the green-light-blending blend for the problem that the energy gap of the red-light-blending blend is excessively inefficient and the intermolecular energy shift cannot be efficiently performed. In view of the energy gap, it is possible to efficiently move the agonist energy of the main material to the calendering blend to form a very high efficiency luminescent layer. Thus, the present invention is a luminescent layer which can constitute a high efficiency and has a long life. And when 'Ar2 is a substituted or unsubstituted benzene ring, or a substituted or unsubstituted 2,7-phenanthryl or tribenzophenone ring, [Ra-Ar1-] and [Rb-Ar3-] have the same structure. The symmetry of the base time 'molecularity increases crystallinity, and it is difficult to maintain high non-crystallinity during film formation. In contrast, in the present invention, [Ra-Ar1 -] and [Rb-Ar3-] have a structure different from each other, thereby preventing crystallization. Wherein the triplet energy gap constituting the material of the organic electroluminescent element -15-200918640

Eg ( Τ ) may be exemplified by a luminescence spectrum, and examples thereof include the following. Specifically, each material was dissolved in an EPA solvent (diethyl ether: isopentane: ethanol = 5:5:2 in a volume ratio) at 10 #mol/L, and used as a sample for calender measurement. The sample for calender measurement was placed in a quartz container, cooled to 77 K, and irradiated with a laser to measure the wavelength of the emitted neon light. For the connection line of the short-wavelength side rise of the obtained neon spectrum, the wavelength 値 at the intersection of the connection line and the bottom line (absorption zero) is converted into energy 値 as the triplet energy gap Eg (T). For the measurement, for example, a commercially available measuring device F-45 00 (Hitachi) can be used. However, the present invention is not limited thereto, and may be defined as a triplet energy gap without departing from the gist of the present invention. In the above formula (1), when Ra, Rb, Ar1, Ar2 or Ar3 has one or a plurality of substituents, the substituent is an aryl group having 6 to 22 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or carbon. The halogenated alkyl group having 1 to 20, the cycloalkyl group having 5 to 18 carbon atoms, the carboxyalkyl group having 3 to 20 carbon atoms, a cyano group or a halogen atom have no nitrogen atom, so that the main component can be further improved. The stability of the material and the longer life of the component. Among them, each of Ra, Rb, Ar1, Ar2 or Ar3 has 2 or less substituents, and preferably 1 or less. Examples of the aryl substituent having 6 to 22 carbon atoms include a phenyl group, a fluorene-16-200918640 phenyl group, a triphenylene group, a naphthyl group, a phenylnaphthyl group, a naphthylphenyl group, and a naphthylnaphthyl group. Phenylphenanthryl, fluoranthenyl, 9,10-dialkylfluorenyl, 9,10-diarylindenyl, trimethyl, phenanthrenyl, dibenzofuranyl are preferred. Preferred is a phenyl 'biphenyl group having a carbon number of 6 to 18, a triphenylene group, a naphthyl group, a phenylnaphthyl group, a naphthylphenyl 'fluoranthyl group, a 9,10-dimethylindenyl group, and a triple extension. Methyl, phenanthryl, dibenzofuranyl. More preferably, it is a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group or a dibenzofuranyl group having a carbon number of 6 to 14. Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an η-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, and an n-pentyl group. , η_hexyl, η-heptyl, η-octyl, η-fluorenyl, η-fluorenyl, η-undecyl, η-dodecyl, η-tridecyl, η-fourteen Alkyl, η-pentadecyl, η-hexadecyl, η-heptadecyl, η-octadecyl, neopentyl, hydrazine-methylpentyl, 2-methylpentyl, 1 _Pentylhexyl, 1-butylpentyl, hydrazine-heptyloctyl, 3-methylpentyl, and the like. Examples of the halogenated alkyl group having 1 to 20 carbon atoms include a chloromethyl group; [-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, and 1, 3-Dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromo Isobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, i,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-t-butyl, 1,2,3-triiodopropyl and the like. Examples of the cycloalkyl group having 5 to 18 carbon atoms include a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a 3,5-tetramethylcyclohexyl group, and the like, and a cyclohexyl group, a cyclooctyl group, and the like are also mentioned. , 5-tetramethylcyclohexyl and the like. -17- 200918640 As a methylidene group having a carbon number of 3 to 20, for example, an alkylmercaptoalkyl group, an arylalkylene group, or an aralkylcarboxyalkyl group is preferable, and trimethylmethane can be mentioned as an example. , triethylmethyl decyl, tributyl methoxyalkyl, trioctyl methoxyalkyl, triisobutyl methoxyalkyl, dimethyl ethyl methacrylate, dimethyl isofuranyl mercaptoalkyl, dimethyl Propylmercaptoalkyl, dimethylbutylmethanyl, dimethyl tert-butylcarboxyalkyl, diethylisopropylformamidinyl, phenyldimethylformamidinyl, diphenylmethylformamidine , diphenyl tert-butylcarboxyalkyl, triphenylcarbenyl, and the like. The halogen atom may, for example, be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. In the above formula (1), when Ar2 is a substituted or unsubstituted benzene ring or a substituted or unsubstituted 2,7-phenanthryl group or a tribenzobenzene ring, Ar1 and Ar3 are mutually different aromatic hydrocarbon groups. good. Or Ar1 and Ar3 are preferably condensed aromatic hydrocarbon groups different from each other. Thereby, [Ra-Ar1-] and [Rb-Ar3-] are different structures, and crystallization during film formation can be prevented. Further, since Ar1 and Ar3 are selected from the group consisting of an aromatic smog group and a condensed aromatic hydrocarbon group, the number of core atoms in the skeleton portion can be ensured to ensure the stability of the molecule. In addition, energy can be moved to the pray light blend because moderately excited triplet energy is available. And 'has the effect of actually preventing crystallization. When a green calendering material is used in combination, a highly efficient and long-life organic electroluminescent device can be constructed. In the above formula (1), at least the anthracene of Ra and Ar1 is substituted or unsubstituted phenanthrene ring. Further, in the above formula (1), Ra is a substituted or unsubstituted phenanthrene ring, -18-200918640

Ar is preferably a substituted or unsubstituted benzene ring. Further, in the above formula (1), it is preferred that Ra is a substituted or unsubstituted phenanthrene Ar1 system, and a substituted or unsubstituted benzene ring is preferred. By selecting the ring structure, it is possible to form a film for an organic light-emitting element excellent in stability, and in particular, a green light-emitting material can be used for high-efficiency, long-life components. In the present invention, the excitation triplet energy of the main material is preferably 2 or more and 2.8 eV or less. The triplet energy is only 2.4 eV or more, and the energy of the phosphorescent material that emits light below 48 〇 55 55 〇 nm can be performed. 2 _ 8 e V or less 'avoidable (4) The problem that the energy gap of the green pity conjugate can not be efficiently emitted. Further, the excited triplet energy of the main material is more preferably 2 e e e e or more, and more preferably 2.5 eV or more and 2 _ 7 eV or less. As a main material of the present invention, for example, a giant ring can be cited as an electrostructure: .4 eV or more is only an excessively large, 7 eV example.

-19- 200918640

B-39 B-40

-20- 200918640

In the present invention, the phosphorescent material contains a metal complex, and the metal complex is preferably a metal atom and a ligand selected from the group consisting of Ir, Pt, Os, Au, Cu, Re, and Ru. Particularly, it is preferred that the aforementioned ligand has a primary metal bond. From the viewpoint that the quantum yield of the light is high, and the external quantum efficiency of the light-emitting element can be further improved, it is preferable to use a compound containing a metal selected from the group consisting of iridium (Ir), hungry (Os), and platinum (Pt). Metal complexes such as hunger bodies and aluminum morphs are better, among which 铱 体 and platinum 错 are better, and the original metal ruthenium is the best. -21 - 200918640 The following is a specific example of the best metal wrong body, in which the luminescent light is a green to red metal complex.

-22 200918640

In the present invention, at least one of the above-mentioned phosphorescent materials contained in the light-emitting layer is preferably a light-emitting wavelength of 480 nm or more and 580 nm or less. The maximum wavelength of the emission wavelength is preferably 5 OO nm or more and 5 5 Onm or less. When a luminescent material (phosphorescence blend) having such an emission wavelength is blended with a specific host material used in the present invention to constitute a light-emitting layer, a highly efficient organic electroluminescence device can be obtained. The organic electroluminescence device of the present invention has a hole transport layer (hole injection layer), and the hole transport layer (hole injection layer) may preferably contain the material for an organic electroluminescence device of the present invention, and the present invention The organic electroluminescence device has an electron transport layer and/or a hole barrier layer, and the electron transport layer and/or the hole barrier layer may preferably contain the material for an organic electroluminescence device of the present invention. The organic electroluminescent device of the present invention preferably has a reducing blend at the interface region between the cathode and the organic thin film layer. Such a structure is intended to improve the luminance or long life of the light in the organic electroluminescence element. The reducing blend may be at least one selected from the group consisting of an alkali metal, a metalloid, an alkali metal compound, an alkaline earth metal, and an alkaline earth metal.

-23- S 200918640 , Alkaline earth metal compounds, rare earth metals, rare earth metal complexes, and rare earth metal compounds. Examples of the alkali metal include Na (work function: 2.36 eV), κ (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: l_95 eV), and the work function is 2_9 eV or less. It is especially good. Preferred among them are K, Rb and Cs, more preferably Rb or Cs, and most preferably Cs. Examples of the alkaline earth metal include Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), Ba (work function: 2.52 eV), and the work function system is 2.9 e V or less. Very good. Examples of the rare earth metal include Sc, Y, Ce, Tb, and Yb, and those having a work function of 2.9 eV or less are particularly preferable. Among the above metals, the reducing ability of the preferred metal is extremely high, and the addition of a small amount to the electron injecting region can increase the luminance or long life of the organic electroluminescent device. Examples of the alkali metal compound include alkali oxides such as Li20, Cs20 and K20, and alkali halides such as LiF, NaF, CsF and KF. LiF, Li20 and NaF are preferred. Examples of the alkaline earth metal compound include BaO, SrO, CaO, and BaxSri-x® (0<χ<1), BaxCabxO (0<χ<1), and the like, and BaO, SrO, and CaO are preferred. Examples of the rare earth metal compound include YbF3, ScF3, Sc03, Y2〇3' Ce2〇3, GdF3, and TbF3, and YbF3, ScF3, and TbF3 are preferred. As an alkali metal complex, an alkaline earth metal complex, or a rare earth metal complex-24-200918640, it is only required to contain at least one alkali metal ion, alkaline earth metal ion, or rare earth metal ion as each metal ion. There is no particular limitation. Further, the ligand is quinolol, benzoparaphenol, acridine phenol, phenanthroline, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl oxadiazole, hydroxydiaryl thiazide Azole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyperborane, bipyridine, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, /3-diketone It is preferred that the imines and their derivatives are not limited thereto. The addition form of the reducing blend is preferably such that a layered or island shape is formed in the interface region. As a method of forming, it is preferred to vapor-deposit a reducing blend by a resistance heating vapor deposition method while vapor-depositing an organic material which forms a light-emitting material or an electron injecting material in an interface region, and disperses a reduced blend in an organic substance. The molar ratio of the molar ratio is organic: the reducing blend = 100:1 to 1:100, preferably 5: i to i: 5. When the reducing blend is formed into a layer shape, after the luminescent material or the electron injecting material of the organic layer of the interface is formed into a layer, the reducing blend is separately vapor-deposited by resistance heating evaporation, preferably forming a layer thickness. 〇1~15 nm. When the pyrogenic blend is formed into an island shape, after the luminescent material or the electron injecting material of the organic layer of the interface forms an island shape, the reducing blend is separately vapor-deposited by a resistance heating evaporation method, preferably forming an island. The thickness is 〇〇5~lnm. Further, in the organic electroluminescence device of the present invention, as the ratio of the main component to the reducing blend, the main component of the molar ratio: the reducing blend = 5:1 to 1:5 is preferable, 2:1 ~1:2 is better. The organic electroluminescence device of the present invention has an electron injecting layer of -25 to 200918640 between the light emitting layer and the cathode, and the electron injecting layer contains a nitrogen-containing ring derivative as a main component. Among them, the electron injecting layer can also serve as a functional layer of the electron transporting layer. In addition, "the main component" means that the electron injecting layer contains 50% by mass or more of the nitrogen-containing ring derivative. The electron injecting layer or the electron transporting layer is a layer that assists electron injection into the light emitting layer, and its electron mobility is large. The electron injection layer is set to moderate the rapid change in energy level and adjust the energy level. As the electron transporting material used for the electron injecting layer, an aromatic heterocyclic compound containing one or more hetero atoms in the molecule is preferably used, and a nitrogen-containing cyclic derivative is particularly preferable. Further, as the nitrogen-containing ring derivative, an aromatic ring having a nitrogen-containing 6-membered ring or a 5-membered ring skeleton or a fused aromatic ring compound having a nitrogen-containing 6-membered ring or a 5-membered ring skeleton is preferred. As the nitrogen-containing ring derivative, for example, a nitrogen-containing cyclic metal-chelating complex represented by the following formula (A) is preferred.

R2 to R7 each independently represent a hydrogen atom, a halogen atom, an oxy group, an amine group, a ketone group having a carbon number of 1 to 40, a oxime group, a aryloxy group, a thiol group, or a heterocyclic group. Was replaced. Examples of the halogen atom include fluorine, chlorine, bromine, and iodine. Further, -26 to 200918640 may, for example, be an alkylamino group, an arylamino group or an aralkylamine group as an amino group which may be substituted. The hydrocarbon group having 1 to 40 carbon atoms may, for example, be a substituted or unsubstituted alkyl group, an alkenyl group, a cycloalkyl group, an aryl group or an aralkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an η-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an η-pentyl group, an η-hexyl group, and η. -heptyl, η-octyl, η-fluorenyl, η-fluorenyl, η-undecyl, η-dodecyl, η-tridecyl, η-fourteenth, η-ten Five-family base, η-sixteen yard base, η-seventeen yard base, η-eighteen yard base, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1 -butylpentyl, 1-heptyloctyl, 3-methylpentyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxy Base, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl, chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromine Methyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t- Butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3- two Isopropyl, 2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-amino Isobutyl, 1,2-aminoethyl, 1,3 - _aminopropyl, 2,3-diamino-t-butyl, 1,2,3-triaminopropyl , cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3 - _ chloropropyl, 2,3 - _ cyano-1-yl-'1-butyl, 1,2,3-diaminopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 1,2-dinitrate Base, -27- 200918640 2,3-dinitro-bubutyl, 1,2,3-trinitropropyl and the like. Preferred among them are methyl, ethyl, propyl, isopropyl, η-butyl, s-butyl, isobutyl, t-butyl, η-pentyl, η-hexyl, η-heptyl , η-octyl, η-fluorenyl, η-fluorenyl, η-undecyl, η-dodecyl, η-tride, η-fourteenth, η-fifteen , η -16 yard base, η -17 yard base, η-eighteen yard base, neopentyl, 1-methylpentyl, 1-pentylhexyl, or 1-butylpentyl, 1- Heptyl octyl. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a 1-methylvinyl group, and a benzene group. Vinyl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-propenylpropyl, 3-propenylpropyl, 3,3-phenylenepropyl, 1,2-methylpyrrolyl, 1-ben The base-1-butyring group and the 3-phenyl-1-butyl group % are preferably a styryl group, a 2,2-diphenylvinyl group, a 1,2-diphenylvinyl group or the like. Examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a 3,5-tetramethylcyclohexyl group, and the like, and a cyclohexyl group, a cyclooctyl group, and a 3,5-tetramethylcyclohexyl group. good. The alkoxy group is a group represented by -ΟΥ. Specific examples of the anthracene are the same as those described above, and the preferred examples are also the same. Examples of the non-condensed aryl group include a phenyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a p-biphenyl-4-yl group, and a ρ- group. Biphenyl-3-enyl, ρ-bitriphenyl-2-yl, m-bitriphenyl-4-yl, m-bitriphenyl-3-yl, m-biphenyl-2 -yl' oxime-tolyl, m-tolyl, ρ-methyl-28- 200918640 phenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl , 4"-t-butyl-P-biphenyl-4-yl, anthracene- cumenyl, m- cumenyl, P- cumenyl, 2,3-xylyl, 3,4 a - dimethylphenyl group, a 2,5-dimethylphenyl group, a mesityl group, an m-tetraphenyl group, etc. Among them, a phenyl group, a biphenyl-2-yl group, a biphenyl-3-yl group are preferred. ,biphenyl-4-yl, m-bitriphenyl-4-yl, m-bitriphenyl-3-yl, m-bitriphenyl-2-yl, p-tolyl, 3,4 Examples of the -dimethylphenyl group and the m-tetraphenyl-2-ylindole as the condensed aryl group include, for example, a 1-naphthyl group or a 2-naphthyl group. The anthracenyl group is a monocyclic ring or a condensed ring, preferably a core carbon. a heterocyclic group having a number of 1 to 20, preferably a core carbon number of 1 to 12, more preferably a core carbon number of 2 to 10, containing a nitrogen atom and oxygen An aromatic heterocyclic group having at least one hetero atom of a sulfur atom or a selenium atom. Examples of the heterocyclic group include a compound, an acridine, a piperazine, a morpholine, a thiophene, and a selenophene. Furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, hydrazine, oxazole, hydrazine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, evil Diazole, quinoline, isoquineline, pyridazine, naphthalene, quinoxaline, quinazoline, porphyrin, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole The group derived from azole, benzothiazole, benzotriazole, TAI, carbazole, azepine or the like is preferably furan, thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine or quinoline. The pyridazine, naphthium ingot, quinoxaline, quinazoline is preferably a group derived from furan, thiophene, pyridine, or quinoline, more preferably a quinolyl group. Examples of the aralkyl group include a benzyl group. , 丨-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, -29- 200918640 α-naphthylmethyl, Ha-naphthylethyl 2-α·naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl,/5-naphthylmethyl, 1-/3-naphthylethyl, 2-/ 5-naphthylethyl, 1-0-naphthylisopropyl, 2-indolylnaphthylisopropyl, p-methylbenzyl, m-methylbenzyl, fluorenyl-methylbenzyl , ρ-chlorobenzyl, m-chlorobenzyl, fluorenyl-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, anthracene-bromobenzyl, p-iodobenzyl, M-iodobenzyl, oxime-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, fluorenyl-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl , 〇-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, hydrazine-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, fluorenyl-cyano Benzyl, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyl, and the like. Preferred among them are benzyl, P-cyanobenzyl, m-cyanobenzyl, fluorene-fluorenylmethyl, 1-benzylethyl, 2-benylethyl, 1-phenyl Isopropyl, 2-phenylisopropyl. The aryloxy group is represented by -OY', and examples of Y' include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 9-fluorenyl group, and a 1- Phenylidene, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-butanyl, 2-butyl, 9-butyl, 1-indenyl, 2-indenyl 4-mercapto, 2-biphenyl, 3-linked base, 4-bonded base, p-biphenyl-4-yl, p-biphenyl-3-yl, p-linked Phenyl-2-yl, m-biphenyl-4-yl, m-bitriphenyl-3-yl, m-biphenyl-2-yl, anthracene-tolyl, m-tolyl, P-tolyl, pt-butyl base, p-(2-propenylpropyl) benzyl, 3-methyl-2-nyl, 4-methyl-1-naphthyl, 4-methyl-1- Mercapto, 4'-methylbiphenyl, 4"-t-butyl-P-biphenyl-4-yl, etc. -30- 200918640 aryloxy heteroaryloxy is -OZ 'Expression, as an example of Z', a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-mercapto group, a 3-anthracene Sulfhydryl, 4 - fluorenyl, 5 - Π bow ID, 6 - D, D, 7 - D D, 1, 1 - Π, 3 - different! , 4-isodecyl, 5-isodecyl, 6-isodecyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzo Furanyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-iso Benzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinoline Lolinyl, 6-quinolyl, 7-quinolyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolyl, 4-isoquinolinyl, 5-isoquinolinyl, 6 -isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-oxazolyl, 2-hydrazine Azyl, 3-oxazolyl, 4-oxazolyl, 1-phenanthryl, 2-phenanthryl, 3-nonyl, 4-undecyl, 6-non-H-yl, 7-non Indole, 8-undecyl, 9-phenanthryl, 1 fluorenyl, 1 -acridinyl, 2 -acridinyl, 3-anridinoyl, 4-acridinyl, 9-acridine 1,1,phenanthroline, 2,yl, 1,7-phenanthroline-3-yl, 1, 7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7- Phenanthroline-9-yl, 1,7-phenanthroline-10-yl, 1.8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline- 4-Based, 1,8-non-cyclolin-5-yl, 1,8-non-cyclolin-6-yl, 1,8-non|Benlin-7-yl, 1,8-phenanthroline-9 _, 1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl, 1.9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1 , 9-phenanthroline-5-yl, 1.9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, -31 - 200918640 1 , 9-phenanthroline-10-yl, 1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1, 1 0 -phenanthroline-5-yl, 2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9 -phenanthroline-5-yl, 2.9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2.9-phenanthroline-10 -yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2.8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2 , 8-phenanthroline-6-yl, 2.8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl 2.7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2.7-phenanthroline-5-yl, 2,7-phenanthrene啉-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-1 0-yl, 1-phenazinyl, 2 - phenazinyl, 1-phenothiazine, 2-phenothiazine, 3-phenothiazine, 4-phenothiazine, 1-phenoxazinyl, 2-phenoxazinyl, 3-anteno Oxazinyl, 4-phenyloxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furenyl, 2 -Thienyl, 3-thiol, 2-methylpyrrole-:1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5- , 3-methylpyrrolidin-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrole-4-yl, 3-methylazul-5-yl, 2-t-butyl -4 -yl, 3-(2-phenylpropyl)pyrrole-1 -yl, 2-methyl-1-indenyl, 4-methyl-1-indenyl, 2-methyl- 3-indenyl, 4-methyl-3-indolyl, 2-t-butylindolyl, 4-t-butyl 1-indole, 2-t-butyl 3-卩 卩 卩 、, 4-t-butyl 3- 卩 卩 卩 基 。 。. The alkoxycarbonyl group is represented by -COOY', and examples of Y' include the same as the above alkyl group. The alkylamino group and the aralkylamine group are represented by -NC^Q2. Specific examples of Q1 and Q2 include the same as the above-described alkyl group and the above-mentioned aralkyl group-32-200918640. One of Q1 and Q2 may be a hydrogen atom. The arylamine group is represented by -N A r 1 A r 2 , and specific examples of A r 1 and A r 2 include the same groups described for each of the above-mentioned non-condensed aryl group and condensed aryl group. One of the eight... and Ar2 may be a hydrogen atom. Μ为铭(A1), gallium (G a ) or indium (I η ), preferably I η. L of the above formula (Α) is a group represented by the following formula (Α,) or (Α,,). R8 R9

R12 R”

In the above formula, 'R8 to R12' each independently represent a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and a mutually adjacent group may form a cyclic structure. Further, each of R13 to R27 independently represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 4 carbon atoms, and a mutually adjacent group may form a cyclic structure. Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R8 to R12 and R13 to R27-33 to 200918640 of the above formula (A) and formula (A") include the same specific examples of R2 to R7. Examples of the divalent group in the case where R12 and R13 to R27 form a cyclic structure adjacent to each other include tetramethyl, pentamethyl, hexamethyl, diphenylmethane-2,2'-diyl. Diphenylethane-3,3'-diyl, diphenylpropane-4,4'-diyl, etc. Specific examples of the nitrogen-containing cyclic metal chelate complex represented by the above formula (A) are as follows, However, it is not limited to their exemplified compounds. -34- 200918640

(A-2) (A-4)

(A-6) (A-8)

(A-10) (A-12)

(A-14)

(A-16) -35- 200918640

(A-17)

(A-18)

(A-19)

36- 200918640

(A-31)

(A-32)

(A-33)

(A-34)

(A-35)

(A-36) The electron injecting layer or the electron transporting layer in the present invention is preferably one containing a nitrogen-containing heterocyclic derivative. The electron injecting layer or the electron transporting layer is a layer that assists electron injection into the light emitting layer, and its electron mobility is large. The electron injection layer is set to moderate the rapid change in energy level and adjust the energy level. As a material used in the electron injection layer -37- 200918640 in the layer or electron transport layer, can the 8-hydroxyquinoline be used? It is preferred to use a metal complex, a oxadiazole derivative, or a nitrogen-containing heterocyclic derivative. Specific examples of the metal complex of the above 8-hydroxyquinoline or a derivative thereof include a metal chelate oxynoid compound containing oxine (normally 8-quinolinol or 8-hydroxyquinoline), for example, A ginseng (8-quinolinol) aluminum can be used. The following are the oxadiazole derivatives.

Ar22

In the above formula, 'Ar17' Ar18, Ar19'Ar21, Ar22 and Ar25 represent an aryl group having or not having a substituent, and Ari7 and Ar18, Ar19 and Ar21, and Ar22 and Ar25 may be the same or different from each other. Αγ2〇, Αγ23 and Ar24 represent an extended aryl group with or without each substituent, and Ar23 and Ar24 may be the same or different from each other. Further, as the aryl group, a phenyl group, a naphthyl group, a phenyl group, a hydrazine group, a hydrazine group, a hydrazine group, and the like can be given. Further, examples of the substituents thereof include an alkyl group having 1 to 10 carbon atoms, a tertiary alkyl group having a carbon number of 丨10, and a cyano group. As the electron-transporting compound, those having good film formability can be used. Specific examples of these electron-transporting compounds include τ $ #. -38- 200918640

The nitrogen-containing heterocyclic derivative may, for example, be a nitrogen-containing heterocyclic derivative having an organic compound of the following general formula, instead of a metal-containing compound containing a metal complex. For example, a 5-membered ring or a 6-membered ring containing the skeleton shown in (A) or a structure shown in (B) may be mentioned.

N

In the above (B), X represents a carbon atom or a nitrogen atom. Zi and Z2 each independently represent a group of atoms which can form a nitrogen-containing hetero ring. -39- 200918640

(C) It is preferably a nitrogen-containing aromatic polycyclic organic compound having a 5-membered ring or a 6-membered ring. Further, in the case of the nitrogen-containing aromatic polycyclic group having such a plurality of nitrogen atoms, the nitrogen-containing aromatic polycyclic organic compound having the skeleton of the above (A) and (B) or (A) and (C) is combined. The nitrogen-containing group of the nitrogen-containing organic compound is, for example, selected from a nitrogen-containing heterocyclic group represented by the following general formula. -40- 200918640

In the above formulae, R is an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms, and η is 〇. An integer of 〜5, η is an integer of 2 or more, and R of the plural numbers may be the same or different from each other. Further, as a preferable specific compound, a nitrogen-containing heterocyclic derivative represented by the following formula may be mentioned. HAr-L1 - In the above formula, HAr is a nitrogen-containing anthracene ring L 3 which is a good w + and has a carbon number of 3 to 40 with a substituent, and has a carbon number of 6 to 40 which may have a π K group. An aryl group or a heterocyclic aryl group having a carbon number of 3 to 4 η & 〇 having a substituent, Ar 1 being a 2 僭苌 + 、 、 、 、 、 、 、 、 、 、 An aryl group having a carbon number of 6 to 40 having a substituent or a heteroaryl group having a carbon number of 3 to 40 having a substituent. HAr is, for example, one selected from the group consisting of the following. -42- 200918640

L1 is, for example, a group selected from the group consisting of the following.

Ar2 is, for example, one selected from the group consisting of the following. -43- 200918640

Ar1 is, for example, an arylsulfonyl group which may be selected from the following.

In the above formula, each of R1 to R14 is independently a hydrogen atom, a halogen atom, a fluorenyl group having 1 to 20 carbon atoms, a oxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, or a substituent. The aryl group having 6 to 40 carbon atoms or the heteroaryl group having 3 to 40 carbon atoms, and Ar3 is an aryl group having 6 to 40 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms which may have a substituent. Further, in Ar1 represented by the above formula, all of R1 to R8 are a nitrogen-containing nitrogen-containing heteropoly-44-200918640 ring derivative. Others may also use the following compounds as well. R*! X2 R2-n^^n-r4X1 R3 Refer to JP-A-9-3 448. In the above formula, R! to R4 each of the valleys II represents a hydrogen atom, a substituted aliphatic group, a substituted or uncapped part. 1 hydrazine-substituted aliphatic cyclic group-substituted carbocyclic aromatic ring group, taken in the decene + intrinsic substituted or unsubstituted heterocyclic: X2 each independently represents an oxygen atom, a sulfur atom or a dicyanomethyl group Or the unsubstituted or unsubstituted group, X], or the following compound can also be used. Reference special opening 2000-173774

In the above formula, R1, R2R and R4 may be the same or different from each other in the aryl group represented by the following formula.

-45- 200918640 In the above formula, R5, R6, R7, R8 and R9 may be the same or different hydrogen atoms, or at least one of them each being a saturated or unsaturated alkoxy group, a deutero group, an amine group or an alkylamine. base. Further, it may be a high molecular compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative. Further, the electron transporting layer is preferably at least one of the nitrogen-containing heterocyclic derivatives represented by the following formulas (201) to (203).

R1 L Ar1—Ar2 · · · (201)

Ar3—

N • · · (20B) y~n2

N \ R3 In the above formula (201) to (2〇3), R is a hydrogen atom, an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, and a substituent a quinolyl group, an alkyl group having a carbon number of a substituent, or an alkoxy group having a carbon number which may have a substituent, η is an integer of 〇~4, and R is an aryl group having 6 to 15 carbon atoms which may have a substituent a pyridyl group which may have a substituent, a quinolyl group which may have a substituent, a C fluorenyl group having a carbon number of 12 Å or a oxy group having 1 to 20 carbon atoms, and R 2 and R 3 each independently - 46 - 200918640 W is a hydrogen atom, a pyridyl group having a substituted carbon number of 6 to 6 fluorene having a substituent, a quinolyl group having a substituent of nJ, and an I h group Carbon number </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; a pyridyl group having a substituent, a coordinating group having a substituent, or a substituent of a substituent, Arl being a carbon number I ^ which may have a substituent, a stretching group having a substituent, or The -orolinyl ' Α ' which may have a substituent: a 6 to 6 fluorene aryl group which may have a substituent, a pyridyl group which may have a substituent, and a quinoline having a substituent The group may have an alkyl group having a carbon number of 1 to 20 or a carbon number alkoxy group which may have a substituent. The aryl group having 6 to 6 Å carbon atoms which may have a substituent, the quinolinyl group which may have a substituent, or the substituent which may have a substituent. The base of the formula, the carbon number which may have a substituent, the oxime group which is awkward, and the group represented by 磲-ΑΓΐ-ΑΡ (Arl and Αγ2 are each the same as described above). Further, in the above formulae (201) to (203), R is a hydrogen atom, an aryl group having 6 to 6 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, and a quinolyl group having a substituent. An alkyl group having a carbon number of a substituent or a courtoxy group having 1 to 20 carbon atoms which may have a substituent. The aryl group having 6 to 60 carbon atoms is preferably an aryl group having 6 to 4 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms, and specific examples thereof include a phenyl group, a naphthyl group, and an onion group. Fiji, butyl, ketone, sulfhydryl, biphenyl, triphenylphenyl, t-butylphenyl, (2-phenylpropyl)phenyl, fluoranthenyl, fluorenyl, snail A monovalent group, a perfluorophenyl group, a perfluoronaphthyl group, a perfluoro-47-200918640 ketone group, an all-gas biphenyl group, a 9-phenyl hydrazine, a monovalent group, 9_ (〗, -Naphthyl)-based monovalent group, 9-(2'-naphthyl)anthracene-based monovalent group, 6-phenyl-based monovalent group, 9-[4-(diphenylamino)phenyl group The monovalent group formed by 蒽 is phenyl, naphthyl, biphenyl, terphenyl, 9-( 10-phenyl)-enyl, 9-[1〇-(1,-naphthyl) ] Mercapto, 9-[1〇-(2,-naphthyl)]indenyl, etc. are preferred. The alkyl group having 1 to 6 carbon atoms is preferably a butyl group, a pentyl group or a hexyl group. The carbon number is 3 or more, and the alkyl group having 1 to 20 carbon atoms may be used. Specific examples thereof include methyl group and ethyl group. Examples of the group and the propyl group include a halogenated alkyl straight chain, a ring or a branch such as a trimethylmethyl group. The alkoxy group having 1 to 20 carbon atoms is preferably an alkoxy group having 1 to 6 carbon atoms, and specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentyloxy 'hexyl group. The oxy group or the like having a carbon number of 3 or more may have a linear chain, a ring shape or a branch. The substituent of each group represented by R may, for example, be a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, a k-oxy group having 1 to 2 carbon atoms which may have a substituent, and may have a substituent. The aryloxy group having 6 to 4 carbon atoms, the aryl group having 6 to 40 carbon atoms which may have a substituent, or the heteroaryl group having 3 to 40 carbon atoms which may have a substituent. Examples of the halogen atom include fluorine, chlorine, bromine, and the like. The alkyl group having 1 to 20 carbon atoms, the alkoxy group having 1 to 2 carbon atoms, and the aryl group having 6 to 40 carbon atoms are the same as those described above. Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group and a biphenyloxy group. -48- 200918640 Examples of the heteroaryl group having 3 to 40 carbon atoms include a pyrrolyl group, a furyl group, a thiol group, a S i丨〇丨y 1 group, a pyridyl group, a quinolyl group, an isoquinolyl group, and the like. Benzopyranyl, imidazolyl, pyrimidinyl, oxazolyl, selenylphenyl, oxadiazolyl, triazolyl, and the like. η is an integer of 0 to 4, and 〇~2 is preferred. In the above formula (201), R1 is a aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, a quinolyl group which may have a substituent, and a carbon number which may have a substituent 1~ 20 alkyl or alkoxy 1 to alkoxy. Specific examples of the respective groups' are preferably the same as those described for R as a preferred carbon number and substituent. In the above formulae (202) and (203), R 2 and R 3 each independently represent a hydrogen atom, an aryl group having 6 to 6 carbon atoms which may have a substituent, a fluorenyl group having a substituent, and may have a substituent. The quinolyl group, a carbon number of 1 to 20 which may have a substituent, or an alkoxy group having 1 to 20 carbon atoms which may have a substituent. Specific examples of each of these groups include the same as those described in the above R, as preferred carbon numbers and substituents. In the above formula (201), the aryl group of 6 to 60, the quinolinyl group of the substituent, or (203), L is a pyridyl group which may have a substituent and the carbon may have a substituent or may be A thiol group having a substituent.

The substituent of each group is preferably an extended aryl group having a aryl group having 6 to 40 carbon atoms, and specific examples thereof include a valent group formed by one hydrogen atom of L. The same as L described above can be cited as L. -49- 200918640 Further, L represents a group selected from the group consisting of the following groups.

In the above formula (201), Ar1 is a aryl group having 6 to 60 carbon atoms which may have a substituent, a stretched pyridyl group which may have a substituent, or a quinacridyl group which may have a substituent. The substituents of the respective groups represented by Ar1 and Ar3 include the same as those described for the above respective R. Further, Ar1 is preferably any one selected from the group consisting of condensed ring groups represented by the following formulas (101) to (10). -50- 200918640

(101) (102)

In the above formulas (101) to (110), each of the condensed rings may have a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and may have The bonding group of the aryloxy group having 6 to 40 carbon atoms of the substituent, the aryl group having 6 to 40 carbon atoms which may have a substituent, or the heteroaryl group having a carbon number of 3 to 40 which may have a substituent may be bonded. When the binding group is plural, the binding groups may be the same or different from each other. Specific examples of the respective bases are the same as those described above. In the above formula (110), L' is a single bond or a group selected from the group below. -51 - 200918640

The above formula (103) represented by Ar1 is preferably a condensed ring group represented by the following formulas (111) to (125).

(111) (112) (113) (114)

(119) (120) (121) (122)

(123) (124) (125) -52- 200918640 In the case of (m) to (125), each condensed ring may be a halogen atom, a substituent having a carbon number of 20, and may have a substituent. An alkoxy group having 1 to 2 carbon atoms, an aryloxy group having 6 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 40 carbon atoms which may have a substituent or a carbon number which may have a substituent of 3 to 40 When the bonding group formed by the heteroaryl group of 40 is bonded, or when the binding group is plural, the binding groups may be the same or different from each other. Specific examples of the respective bases are the same as those described above. In the above formula (201), Ar2 is an aryl group having 6 to 6 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, a quinolyl group which may have a substituent, and a carbon number 可 which may have a substituent. An alkyl group of 2 fluorene or an alkoxy group having 1 to 20 carbon atoms which may have a substituent. Specific examples of the respective groups of xa' are preferably the same as those described for R, as a preferred carbon number and substituent. In the above formulae (2〇2) and (203), Ar3 is a carboxy group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, a porphyrin group which may have a substituent, and may have The alkyl group having 1 to 2 carbon atoms of the substituent, the alkoxy group having 1 to 20 carbon atoms which may have a substituent, or the group represented by _Ari_Ar2 (Afl and Ar2 are each the same as described above). Specific examples of the respective groups' are preferably the same as those described in the above R as a preferred carbon number and substituent. Further, Ar3 is preferably any one selected from the group consisting of condensed ring groups represented by the following formulas (: 126) to (I"). -53- 200918640

(126) (127)

In the above formulae (126) to (I35), each of the condensed rings may have a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and may have a bonding group formed by a aryloxy group having 6 to 40 carbon atoms of a substituent, a aryl group having 6 to 40 carbon atoms which may have a substituent, or a heteroaryl group having 3 to 40 carbon atoms which may have a substituent, Or when the binding group is plural, the binding groups may be the same or different from each other. Specific examples of the respective bases are the same as those described above. In the above formula (135), L' is the same as described above. In the above formulae (126) to (135), R' is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 40 carbon atoms which may have a substituent or may have a substituent. a heteroaryl group having a carbon number of 3 to 40. Specific examples of the respective -54 to 200918640 are the same as those described above.

The general formula (128) represented by Ar3 is preferably a condensed ring group represented by the following formulas (1 36 ) to (158).

(138)

(139) (140)

(141)

(146) (147) R, (148) R, (149) (150)

(151) (152) (153) (154) (155)

(157) (157) (158) -55- 200918640 In the above formulas (136) to (158), each condensed ring may be a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and may have a substituent An alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 4 carbon atoms which may have a substituent, an aryl group having 6 to 40 carbon atoms which may have a substituent or a carbon number which may have a substituent of 3 to 40 When the bonding group formed by the heteroaryl group of 40 is bonded, or when the binding group is plural, the binding groups may be the same or different from each other. Specific examples of the respective bases are the same as those described above. R' is the same as described above. Further, each of Ar2 and Ar3 is independently selected from the group of the following groups.

Specific examples of the nitrogen-containing heterocyclic derivative represented by the above formulas (201) to (203) of the present invention are shown below, but the present invention is not limited to these exemplified compounds. Further, in the following table, Har represents the following structure in the above formulas (201) to (203). -56- 200918640

R1

'^—R2 N

N y~R2 R3 -57- 200918640

-58- 200918640 2-1 2 3 4 5 6 7 8 9 HAr

-59- 200918640 3-1 2 3 4 5 6

Ar2

W ΌΟ

XO

XO

X)D -60- 200918640 HAr——L—Ar1——Ar2

Ai2 HAr

XT οφο Xi〇 οφο xo xr o^o rr οφο x〇 7繁, umbrella cut 8 繁 ♦ cut 9 I, umbrella work 1 ◦ art gx + cut 11

Όα

-61 - 12 5-1 200918640 2 3 4 5 6 HAr

HAr—L—Ar1—Ar2 6-1 2 3 4 HAr

ό

62- 5 200918640

-63- 200918640 8-1 2 3 4 5 6 7 8 9 10 11 12 13 HAr

ΗΑγ—L—Ar1—Ar2 L Ar1 XX '«k

Ό Ό Ό Ό Ό Ό Ό Ό 64- 200918640

-65 - 200918640

-66 - 200918640

6 200918640

-68- 200918640

-69- 5 200918640

-70- 200918640 HAr-L—Ar1—Ar2 16-1 2 3 4 5 6 7 8 HAr L Ar1 Ar2

f-feC -71 - 200918640

In the above specific examples, (1 - 1), (1-5), (1-7), (2-1), (3-1), (4-2), (4-6), ( 7-2), (7- 7), (7-8), (7-9), (9-1), and (9-7) are preferred. Further, the film thickness of the electron injecting layer or the electron transporting layer is not particularly limited, but is preferably 1 to 10 nm. Further, as a constituent component of the electron injecting layer, as a nitrogen-containing ring derivative-72-200918640, it is a genus and a class of A1, and other inorganic compounds of the type A1 are used as insulators or semiconductors. good. The electron injecting layer may be composed only of an insulator or a semiconductor, and it is possible to effectively prevent leakage and improve electron injectability. As the insulator, it is preferable to use at least one metal compound selected from the group consisting of an alkali metal chalcogenide, an alkaline earth metal chalcogenide, an alkali metal halide, and an alkaline earth gold halide. It is preferable that the electron injecting layer is composed only of the alkali metal chalcogenide or the like, so that electron injection can be further improved. Specific examples of the preferred alkali metal chalcogenide include Li20, K20, Na2S, Na2Se, and Na20. Preferred examples of the alkaline earth metal chalcogenide include CaO, BaO, SrO, BeO, and BaS CaSe. Moreover, as a halide of a preferable alkali metal, LiF NaF, KF, LiCl, KC1, and NaCl etc. are mentioned, for example. Further, examples of the preferred alkaline earth metal halide include fluorides such as CaF2, BaF2, SrF2, and MgF2 Be F2, and halides other than fluorides. Further, examples of the semiconductor include oxides, nitrides, or nitrogen oxides containing at least one of Ba, Ca, Sr, Yb, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn. A single or a combination of two or more of the compounds. Further, the inorganic compound constituting the electron injecting layer is preferably a microcrystalline or amorphous insulating film. The electron injecting layer is composed only of these insulating films, and a relatively homogeneous film can be formed, so that defects such as black spots can be reduced. Further, examples of the inorganic compound include an alkali metal chalcogenide, an alkaline earth metal chalcogenide, an alkali metal halide, and an alkaline earth gold halide. When such an insulator or semiconductor is used, the layer preferably has a thickness of -73 to 200918640 to about 0.1 nm to about 15 nm. Further, the electron injecting layer in the present invention preferably contains the above-mentioned reducing blend. The hole injection layer or the hole transport layer (including the hole injection transport layer) may be an aromatic amine compound. For example, an aromatic amine derivative represented by the following general formula (I) may be used as Ar1\Ar3 (1) /N. —L—N Ar2 In the general formula (I), Ar 1 to Ar 4 represent a substituted or unsubstituted 50-nuclear aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted nucleus having a nuclear atom number. Examples of the substituted or unsubstituted aryl group having a core carbon number of 6 to 5 Å include a group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, and a 9-fluorenyl group. _ phenanthryl, 2-phenanthryl, 3_phenanthryl, 4-phenanthryl, 9·phenanthryl, 丨_ butyl, 2_ butyl, j 9 · butyl, 1-initial, 2-indenyl , 4-fluorenyl, 2-phenylbiphenyl, 3-phenylbiphenyl, 4-biphenylyl, b-triphenyl-4-yl, p-bitriphenyl P-biphenyl-2- M, m-biphenyl-4-yl, triphenyl-3-yl, biphenyl-2-yl, fluorenyl-tolyl, cardiotolyl, tolyl

Pt butyl phenyl, p_(2-phenylpropyl)phenyl ' 3 -methyl 2 - quaternylmethyl _U fluorenyl, 4-methyl-1-indenyl, 4,-methyl linkage Phenyl, 4,, _t. butyl p-biphenyl-4-yl, fluoranthenyl, fluorenyl and the like. Examples of the substituted or unsubstituted heteroaryl group having 5 to 5 Å of a nuclear atom include 1 DI+ knowing 比pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridyl group, 3 -卩 ratio _ is · base, 4-pyridyl, 1-indenyl, 2-indenyl, 3 _吲哚-74- 200918640 base, 4 - D lead D base, 5-D noise-induced base, 6 - 卩 哄, 7 - D 引 D base, 1-iso D fluorenyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isodecyl, 6-isoindenyl, 7-isoindenyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuran , 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6- Isobenzofuranyl, 7-isobenzofuranyl, quinolyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8- Quinolinyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinoline Lolinyl, 2-quinoxalinyl, 5-quinoline , 6-quinoxalinyl, 1-oxazolyl, 2-oxazolyl, 3-oxazolyl, 4-n-oxazolyl, 9-oxazolyl, 1-phenanthryl, 2-phenanthryl , 3-phenanthryl, 4-phenanthryl, 6-phenanthryl, 7-phenantidinyl, 8-phenanthryl, 9-phenanthryl, 10-phenanthryl, 1-anthridyl, 2 - aridinyl, 3-arridinyl, 4-acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7 -phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthrene Cyclolin-9-yl, 1,7-phenanthroline-1 0-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthrene Benzin-4-yl, 1,8-phenanthroline-5-yl, 1.8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9- 1, 1.8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1, 9-phenanthrene-5-yl, 1,9-phenanthroline-6-yl, 1.9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthrene Benzene-10-yl, 1,1〇-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1:10-phenanthrene Porphyrin-5-yl 2,9-phenanthroline-diyl, 2,9-phenanthroline-3-yl-75- 200918640, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl , 2,9-phenanthroline _6_yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-1-indole, 2.8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline _4_yl, 2.8-phenanthroline-5-yl, 2,8-phenanthrene咐-6-yl, 2,8-phenanthroline-7_yl, 2.8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline , 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2.7-phenanthroline-6-yl, 2,7 - non-cyclic -8-yl, 2,7-phenanthroline-9-yl, 2.7-phenanthroline-10-yl, 1-phenanthyl, 2-phenazinyl, 丨-phenothiazine, 2_ phenothiphthyl, 3-phenothiazine, phenothiphenyl, ι〇_phenthiamyl, 1_phenoxyl, 2-terminal, 3 - phenazinyl, 4 - phen啰卩Qin, 1 〇-phenothrazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5 _ oxadiazolyl, 3-furenyl , 2 -Thienyl, 3-thiol, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methyl _ 5 -yl, 3-methylpyrrole-1-yl, 3 _methyl sulphate-2 yl, 3-methyllalo-4 yl, 3-methyllazol-5-yl, 2 -t-butyl sulphate, (2_phenylpropyl) fluoren-1-yl, 2-methyl noisy, 4-methyl fluorenyl, 2-methyl-3- fluorene Indenyl, 4-methyl-3- 3 - D fluorenyl, 2 _ t -butyl 1 卩 卩 、, 4-t-butyl 1-indenyl, 2-t-butyl 3-indole Base '4_t_butyl 3_ fluorenyl and the like. Phenyl, naphthyl, biphenyl, anthracenyl, phenanthryl, anthryl, fluorenyl, fluorenyl, fluorenyl and the like are preferred. L is a linking group. Specifically, it is a substituted or unsubstituted aryl group having a core carbon number of 6 to 5 Å, a substituted or unsubstituted heteroaryl group having a core number of 5 to 50, or two or more aryl or heteroaryl groups. The divalent group obtained by the combination of a single bond, an ether bond, a thioether bond, an alkylene group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, and an amine group can be obtained by the combination of -76 to 200918640. Examples of the exoaryl group having a nucleus carbon number of 6 to 50 include hydrazine, 4-phenylene, I, 2-phenylene, 1,3-phenylene, I,4, and 2.6. - anthranyl, 1,5-anthranyl, 9,1 〇 _ 蒽, 9,1 〇 - phenanthrene, 3.6- phenanthrene, 16 - fluorenyl 2, 7 _ 芘6,12-extended fluorenyl, 4,4'-linked phenyl, 3,3,_linked phenyl, 2,2,_linked phenyl '2,7 _ hydrazine and the like. Examples of the extended aryl group having a nuclear atom number of 5 to 50 include 2 s~ thiol phenyl, 2,5-8 丨1〇1 基 1, 2,5-exoxadiazolyl and the like. 14-phenylene, 1,2-phenylene, ι,3-phenylene, 1,4-naphthyl, 9^?1 0 » anthracene, 6,12-extension 4,4,-stretched phenyl, 3,3,-linked phenyl, 2,2'-linked phenyl, 2,7-extended thiol. When L is a linking group of two or more exoaryl or heteroaryl groups, adjacent aryl or aryl groups are bonded to each other via a divalent group to form a new ring. Examples of the divalent group forming the ring include tetramethyl, pentamethyl, hexamethyl, diphenylmethane-2,2,-diyl, diphenylethane-3,3. __ base, diphenylpropane-4,4,-diyl and the like. Examples of the substituent of Ar1 to Ar4 and L include a substituted or unsubstituted aryl group having a core number of 6 to 50, a substituted or unsubstituted heteroaryl group having a number of core atoms of 5% to 5 Å, and a substitution or an unsubstituted group. Alkyl group having a carbon number of 1 to 5 fluorene, a substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 50, a substituted or unsubstituted carbon number of 1 to 5 Å, a substituted or unsubstituted carbon number of 7 5050 aryl fluorenyl, substituted or unsubstituted aryloxy group having 6 to 50 nucleus, substituted or unsubstituted heteroaryloxy group having 5 to 50 nucleus, substituted or unsubstituted nucleocarbon a 6- to 5 fluorene arylthio group, a substituted or unsubstituted heteroarylthio group having 5 to 5 Å of a core atom, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or a non- 77- 200918640 Unsubstituted nuclear atom number, cyano group, nitro group, hydroxy-substituted aryl group with 6-membered aryl group, or substituted or 5- to 50-membered heteroaryl group, halogen _

Examples of the substituted or unsubstituted aryl group having a core carbon number of 6 to 5 Å include a phenyl group, a naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-indenyl group, a fluorenyl group, and a sulfonyl group. 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, anthracene-butyl, 2-butyl, 9-butyl, fluorene-fluorenyl, 2-mercapto, 4_ Mercapto, 2_biphenylfluorene, 3-linked base, 4-butylidene 'p-biphenyl-4-yl, p-bitriphenyl-3-yl, p-biphenyl- 2·yl, m-bitriphenyl-4-yl, m_bitriphenyl-3-yl, m-biphenyl-2-yl, fluorenyl-tolyl, m-tolyl, p•A Stupid, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthoquinone, 4-methyl-1-naphthyl, 4-methyl-i_ Mercapto, 4, methylbiphenyl, 4,-t-butyl-P-biphenyl-4-yl, fluoranthenyl, fluorenyl and the like. Examples of the substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl and 3-pyridyl. , 4·pyridyl, 1-indenyl, 2-indenyl, 3-anthracene, 4-indenyl, 5-nonyl' 6-fluorenyl, 7-fluorenyl, 1- Isoindolyl, 2-isodecyl, 3-isoindolyl, 4-isodecyl, 5 ·isoindolyl, 6-isoindolyl, 7 ·isoindolyl, 2-furan , 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1 -isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, quinolyl , 3-quinolyl, 4-quinolinyl ' 5-quinolinyl' 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, Bu-78- 200918640 isoquinolinyl, 3-iso Quinolinyl, 4-isoquinolyl, 5-isoquinolinyl, quinolyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-phenylenyl, 6-quinoline Porphyrin, 1 -carbazole , 2 -isoxazolyl, 3-carbazole oxazolyl, 9-isoxazolyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthridine _ non-D decyl, 6-non-D 疋, 7-non-D-decyl, 8-nonyl, 9-undetermined phenanthryl, azuldinyl, 2-anridinoyl, 3-anridinoyl, 4-anthranylpyridinyl 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthrene-4-yl, 1,7-phenanthroline-5-yl, 1,7- Phenanthroline-6-yl, 1,7-phenanthroline, 1,7-phenanthroline-9-yl, 1,7-phenanthroline-1 0-yl, 1,8-phenanthrene, 1, ,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthroline, 1,8-phenanthroline-6-yl, 1,8-phenanthroline -7-yl, 1,8-phenanthroline-9 1 , 8 -phenanthroline-1 0-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3. , 9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthroline-6 - 1.9-phenanthroline-7-yl, 1,9-phenanthroline -8-yl, 1,9-phenanthroline-10_ 1,1 0-phenanthroline-2-yl, 1, 1 0-phenanthroline-3-yl, 1, 1 0-phenanthroline, 1 , 10-phenanthroline-5-yl, 2,9-phenanthroline-diyl, 2,9-phenanthroline, 2,9-phenanthroline-4-yl, 2,9-phenanthroline 5-base, 2,9- Rotunolin-6 2.9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-ΙΟ-ΐ 8 -phenanthroline-1 -yl, 2, 8 - phenanthroline-3-enyl, 2,8-phenanthroline-4,2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-phenanthroline -Τ-ΐ 8 - phenanthroline-9-yl, 2,8-phenanthroline-1 0-yl, 2,7-phenanthroline-1 - 2.7-phenanthroline-3-yl, 2,7 -phenanthroline · 4 -yl, 2,7-phenanthroline-5 -2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline -9 - 2.7-phenanthroline-1 0-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazinyl 6-iso-quinoline; 4-; ' 4-, 10-j '9-cycloporphyrin-8-lin-2 · -5-yl-yl, -yl, .yl, -yl,-4-yl-3-yl-yl, yl, yl, yl, yl , base, -79-, 2-200918640 phenothiazine, 3-phenothiazine, 4-phenothiazine, 10-phenothiazine, 1-phenoxazinyl, 2-phenoxazinyl, 3 - phenoxazinyl, 4-phenoxazinyl, 10 0-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxo Diazolyl, 3-furenyl, 2-thiol, 3-thiol, 2-methyl Pyrrol-1-yl' 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrol-1-yl, 3-methyl Pyryrrol-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrol-5-yl, 2 -1 -butylpyrrole-4-yl, 3-(2-phenylpropyl) Q is slightly 1-yl, 2-methyl-1-D-derived D-based, 4-methyl-1-Q-derived D-based, 2-methyl- 3-D-derived D-based, 4-A卩-3-卩引D, 2-t-butyl 1-13, 11-, 4-t-butyl 1-indenyl, 2-t-butyl 3-indenyl, 4- T-butyl 3-mercapto and the like. Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, η-butyl group, s-butyl group, isobutyl group, and t-butyl group. Base, η-pentyl, η-hexyl, η-heptyl, η-octyl, hydroxymethyl, 1-ylethyl, 2-hydroxyethyl, 2-isoisobutyl, 1,2 - _•transethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl , 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3 -trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2, 3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodo Ethyl, 1,3-diiodoisopropyl, 2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2- Aminoethyl, 2-aminoisobutyl, 1,2-aminoethyl, 1,3 -aminopropyl, 2,3-monoamino-t--80- 200918640 butyl, 1,2,3_triaminopropyl, cyanomethyl , 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyanide Base-t-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl , 1,3-dinitroisopropyl, 2,3-dinitro-t-butyl, 1,2,3-trinitropropyl, and the like. Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-golden-based group, and 2 - King Kong Court Foundation, 1 - Freezing Base, 2 - Ice Sheet Foundation Temple. The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms is represented by -? Y. Examples of Y include methyl, ethyl, propyl, isopropyl, η-butyl, s-butyl, isobutyl, t-butyl, η-pentyl, η-hexyl, η-. Heptyl, η-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-Dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2- Dichloroethyl, 1,3_dichloroisopropyl ' 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2- Bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromo Propyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-di Iodine-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-di Aminoethyl, 1,3-diaminoisopropyl, 2,3-amino-t-butyl, 1,2,3-diaminopropyl, hydroxymethyl, 1-cyano Ethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1 2-Diaminoethyl, 1,3 - _aminoisopropyl, 2,3 - fluorenyl-t-butyl, 1,2,3- -81 - 200918640 Tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-t-butyl 1,2,3-trinitropropyl and the like. Examples of the substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-. Phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, ba-naphthylisopropyl, 2-α -naphthylisopropyl, /3-naphthylmethyl, 1-/3-naphthylethyl, 2-/3-naphthylethyl, 1-/3-naphthylisopropyl, 2- /3 -naphthylisopropyl, 1-pyrrolemethyl, 2-(1-pyrrole)ethyl, fluorenyl-methylbenzyl, m-methylbenzyl, fluorene-methylbenzyl, p-chloro Benzyl, chlorobenzyl, fluorenyl-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, fluorenyl-bromobenzyl, P-nonylbenzyl, m-iodobenzyl , 〇-iodobenzyl, P-hydroxybenzyl, m-hydroxybenzyl, fluorenyl-hydroxybenzyl, ρ-aminobenzyl, m-aminobenzyl, fluorene-aminobenzene Methyl, ρ-nitrobenzyl, m-nitromethyl, hydrazine-nitrogen methyl, ρ· benzyl benzyl, m-aminobenzyl, fluorenyl-cyanobenzyl, 1-hydroxy -2-phenylisopropyl, 1-chloro-2-phenylisopropyl and the like. The substituted or unsubstituted aryloxy group having a core carbon number of 6 to 50 is represented by _ Ο Y ', and examples of Y' include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a 1-anthracene group. Base, 2-fluorenyl, 9-fluorenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, pudinyl, 2-butyl, 9- Dicion, 1-indenyl, 2-indenyl, 4-indenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl-p-biphenyl-4-yl, ρ- Biphenyl-3-yl, ρ-bitriphenyl-2-yl, m-biphenyl-4-yl, m-bitriphenyl-3-yl, m-biphenyl-2 -based, fluorene-toluene-82- 200918640 base, m-tolyl, p-tolyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthalene , 4-methyl-1-naphthyl, 4-methyl-1-indenyl, 4'-methyl-based, 4"-t-butyl-p-bi-diyl-4-yl The substituted or unsubstituted heteroaryloxy group having a nuclear atom number of 5 to 50 is represented by -OZ', and examples of Z' include 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-indenyl, 3-indenyl, 4-indenyl, 5-nonyl, 6- Sulfhydryl, 7-fluorenyl, 1-isodecyl, 3-isodecyl, 4-isodecyl, 5-isodecyl, 6-isodecyl, 7-isoindolyl , 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzo Furanyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl , 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolinyl, 2-quinoxalinyl, 5 - quinoxalinyl, 6-quinoxalinyl, 1-oxazolyl, 2-oxazolyl, 3-oxazolyl, 4-n-zolylzoyl, 1-phenanthryl, 2-phenanthryl, 3 _ phenanthryl, 4-phenanthryl, 6-phenanthryl, 7-nonyl, 8-non-U-based, 9-non-D-decyl, 1 0-non-U-based, 1 - Π丫II-based, 2-anridinoyl, 3-anridinoyl, 4-anridinoyl, 9-acridinyl 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1, 7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenanthroline-1 0-yl, 1, 8 -phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl, 1,8-phenanthrene ROUND-83- 200918640 porphyrin-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline-1 0-yl, 1, 9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9- Phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl, 1,10-phenanthrene啉-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl, 2,9-phenanthrene Rotunolin-buyl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline- 6-based, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-1 0-yl, 2,8-phenanthroline-1 -yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5- , 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2 , 7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7 -phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-1 0-yl, 1-phenazine Base, 2-phenazine group, 1-phenothiazine group, 2-phenothiazine group, 3-phenothiazine group, 4-phenothiazine group, 1-phenoxazinyl group, 2-phenyloxazinyl group, 3- phenoxazinyl, 4-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furoxime , 2 -Thienyl, 3-thiol, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole- 5-based, 3-methylpyrrole-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrole-5-yl, 2-t-butyl Oral-4-yl, 3-(2-propenylpropyl)pyridin-1-yl, 2-methyl-1-fluorene-based, 4-methyl-1-indenyl, 2 -Methyl-3-mercapto, 4-methyl-3-indenyl, 2-t-butyl 1-G fluorenyl, 4 -t-butyl 1-B noise-inducing group, 2-t-butyl 3-indenyl group, 4-t-butyl 3-indenyl group and the like. -84- 200918640 A substituted or unsubstituted arylthio group having a core carbon number of 6 to 50 is represented by -SY", and examples of Y" include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and 1 - mercapto, 2-mercapto, 9-fluorenyl, 1-phenanthryl, 2-phenanthrenyl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-butyl, 2-butyl , 9-butyl, 1-indenyl, 2-indenyl, 4-indenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, p-bitriphenyl-4-yl , p-bitriphenyl-3-yl, p-bitriphenyl-2-yl, m-biphenyl-4-yl, m-bitriphenyl-3-yl, m-biphenyl Benzyl-2-yl, fluorenyl-tolyl, m-tolyl, p-tolyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl 4-methyl-1-naphthyl, 4-methyl-1-indenyl, 4'-methylbiphenyl, 4"-t-butyl-P-biphenyl-4-yl and the like. The substituted or unsubstituted heteroarylthio group having a nuclear atom number of 5 to 50 is represented by -SZ", and examples of Z" include 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2- Pyridyl, 3-pyridyl, 4-pyridyl, 2-indenyl, 3-indenyl, 4-indenyl, 5-indenyl, 6-anthracene , 7-fluorenyl, diisodecyl, 3-isodecyl, 4-isodecyl, 5-isodecyl, 6-isoindenyl, 7-isodecyl, 2 - Furanyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2- Quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-iso Quinolinyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoline Lolinyl, 6-quinoxalinyl, 1-oxazolyl, 2-oxazolyl, 3-oxazolyl, 4-oxazolyl-85- 200918640 ' 1 - a non-determined group, 2 - a non-determined group, 3 - a non-determined group ' 4 -a non-decidyl, 6-undecyl, 7-phenanthryl, 8-phenanthryl, 9-phenanthryl, 10-phenanthryl, 1-acridinyl, 2- Acridinyl, 3-anridino, 4-acridinyl, 9- Pyridyl, 1, 7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl, 1 , 8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl, 1,8 -phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline-1 0-yl, 1,9- Phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthrene -6-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl, 1,10-phenanthroline- 2-based, 1, 1 0-phenanthroline·3 -yl, 1, 1 0-phenanthroline-4-yl, 1, 1 0-phenanthroline-5-yl, 2,9-phenanthroline -1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6 -2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl , 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2 , 8-phenanthroline-7-yl, 2,8 -phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthrene Cyclolin-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline -9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazine, 2-phenothiazine, 3-phenylthiazinyl, 4-phenothiazine, 1-phenoxazinyl, 2-phenyloxazinyl, 3-phenyloxazinyl, 4-phenyloxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxo Azolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furenyl, 2-thiol, -86- 200918640 3 -Thienyl, 2-methylpyrrole-1 -yl, 2 -methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyryl-1 -yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrole-5-yl, 2-t-butyl lalid-4-yl, 3-(2-propenylpropyl)-lyl-1-yl, 2 - A certain -1 - D primer, 4-methyl-; 1 - fluorenyl, 2-methyl-3-indenyl, 4-methyl-3-indenyl, 2-t -butyl 1-indole, 4-t-butyl 1-D fluorenyl, 2-t-butyl 3-mercapto 4-1-- butyl 3 - indolyl and the like. The substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms is represented by -C Ο Ο Z, and examples of Z include methyl group, ethyl group, propyl group, isopropyl group, and η-butyl group. Base, s-butyl, isobutyl, t-butyl, η-pentyl, η-hexyl, n-heptyl, η-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl , 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-•trans-t-butyl, 1,2,3-di-propyl Base, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro -t-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1 , 3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2- Iodine isobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-t-butyl, 1,2,3-triiodopropyl 'amine , 1-aminoethyl, 2 - 1 -phenylethyl, 2-aminoisobutyl, 1,2-aminoethyl, 1, 3-diaminoisopropyl, 2,3- Diamino-t-butyl, 1,2,3- Aminopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl , 2,3-dicyano-t-butyl, 1, 2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, -87- 200918640 2 -Nitrate Butyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-t-butyl, 1,2,3-trinitropropyl, and the like. The substituted or unsubstituted aryl group having a core carbon number of 6 to 50 or a substituted or unsubstituted heteroaryl group having a core number of 5 to 50 is represented by -NPQ as P and Q. Examples include phenyl, 1-naphthyl, 2-naphthyl, 1-indenyl, 2-indenyl, 9-fluorenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthrene Base, 9-phenanthryl, 1-butyl, 2-butyl, 9-butyl, 1-indenyl, 2-indenyl, 4-indenyl, 2-biphenyl, 3-biphenyl , 4-biphenylyl, p-bitriphenyl-4-yl, p-bitriphenyl-3-yl, p-bitriphenyl-2-yl, m-bitriphenyl-4- , m-bitriphenyl-3-yl, m-biphenyl-2-yl, fluorenyl-tolyl, m-tolyl, p-tolyl, pt-butylphenyl, p-( 2 -Phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-enyl, 4'-methyl-based, 4" -t-butyl-p-biphenyl-4-yl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-indole Base, 3-mercapto, 4-indenyl, 5-indenyl, 6-fluorenyl, 7-fluorenyl, 1-isodecyl, 3-isodecyl, 4-iso Oryrosyl, 5-iso-D-radoyl, 6-iso-H-indenyl, 7-iso D-indenyl, 2-indolyl, 3-furyl, 2-benzofuranyl, 3-benzo Furanyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-iso Benzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolinyl, 4-quinolinyl, 5-quinoline Lolinyl, 6-quinolyl, 7-quinolyl, 8-quinolinyl, 1-isoquinolyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-iso-sa-D-linyl, 6 ·Iso H-quine, 7-isoindole-based, 8-iso-allinyl, 2-II-quino-88- 200918640 Porphyrin, 5-quinoxalinyl, 6-quinoxalinyl, 1 -carbazolyl, 2-n-day, 3-oxazolyl, 4-oxazolyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthrene, 4-phenanthryl, 6-phenanthryl, 7 -phenanthryl, 8-phenanthryl, 9-phenanthrene, 1 fluorenylpyridinyl, 1-anridinoyl, 2-anridinoyl, 3-anridinoyl, 4-oxanyl, 9-acridinyl 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1 oxalin-4-yl 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenyl-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenanthrene Cyclolin-10-yl, 1,8- phenan-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8 porphyrin·5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-oxolin-9-yl, 1,8-phenanthroline-1 0-yl, 1, 9 - Phenanthroline-2-yl, 1,9- oxalin-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenyl-6-yl 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-oxo-1 0-yl, 1, 1 0-phenanthroline-2-yl, 1 , 1 0-phenanthroline-3-yl, 1, porphyrin-4 -yl, 1, 10 - phenanthroline-5-yl, 2,9-phenanthroline-1 -yl, 2 porphyrin - 3-based, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenyl-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9- phenyl-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2,8-porphyrin -4 -yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-indol-7-yl, 2J-phenanthroline-9-yl, 2 ,8-phenanthroline-10-yl, 2,7-phenyl-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4- , 2,7-phenanthr-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenyl-9-yl, 2,7-phenanthrene Porphyrin-1 0-yl, : 1-phenazinyl, 2-phenazinyl, thiazinyl, 2-phenothiazine, 3-phenothiazine, 4-phenothiazine, 1-azino, 2 - phenoxazinyl, 3-phenyloxazinyl, 4-phenoxazinyl, 2-oxazolylpyridinyl, 7-phenanthroline-phenanthrene-phenanthrene-phenanthrene-ruthenium-phenanthrene-phenanthrene • 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲 菲, 5-oxazolyl, 2-oxadiazolyl, 5-oxo-2-indenyl, 2-thiol, 3-thiol, 2-methylpyrrole-1-yl-3-yl, 2 -methylpyrrol-4-yl, 2-methylpyrrol-5-yl-l-yl-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl-5-yl, 2-t-butyl lado-4 -yl, 3-(2-phenyl-propanyl, 2-methyl-1-D fluorenyl, 4-methyl-1-indole, 2-methyl, 4-methyl-3-indenyl, 2-t-butyl 1-indenyl, 4-t. oleyl, 2-t-butyl 3-indole D, 4-t-butyl 3-D 卩 卩 % Specific compounds of the above general formula (I) of example 7 is not limited to thereto. Sitrate, 3-furfuryl, 2-methylpyryl, 3-methylpyridyl, 3-methylpyridylpyrrol-1-yl-3-yl-3-pyrene-butyl-1-D is shown in Figure 7, but - 90- 200918640

Further, the aromatic amine of the following general formula (II) is also suitable for the formation of a hole injection layer or a hole transport layer.

Ar2

• (II) -91 - 200918640 In the above general formula (II), the definitions of Ar1 to Ar3 are the same as those of Ar1 to Ar4 of the above general formula (I). Specific examples of the compound of the general formula (II) are shown below, but are not limited thereto.

Further, the present invention is not limited to the above description, and the invention is also included in the invention without departing from the scope of the invention. For example, the following changes are also preferred variations of the invention. In the present invention, the light-emitting layer may contain a charge injection auxiliary material. When a light-emitting layer is formed using a main material having a wide energy gap, the difference between the chemical potential (I p ) of the host material and the hole injection, Ip, etc. of the transport layer becomes large. It is difficult to inject the hole in the layer, and it is impossible to obtain sufficient brightness, so that the driving voltage may rise. In this case, when the hole injecting and transporting the charge injecting agent into the light-emitting layer, it is easy to inject the hole into the light-emitting layer, and the voltage can be driven. As the charge injection auxiliary agent, for example, a general hole injection material or the like can be used. Specific examples include triazole derivatives (U.S. Patent No. 3,1,1,1,7, and the like) and bismuth derivatives (Meri 3,1 8,9,4,7, etc.) Reference), the oxime derivative (refer to Japanese Patent Publication No. 37_16096, etc.), and the polyarylalkane derivative (Patent No. 3,615, No. 4, No. 2, No. 3, 82, 989, No. 3, 542, 544, specification, special Japanese Patent Publication No. 45-555, Japanese Patent Publication No. 51-10983, Japanese Patent Publication No. Hei 51-93224, Japanese Patent Publication No. 55-1, No. 56-4 1 48, and Japanese Patent Publication No. 55-J. Japanese Patent Publication No. 56-36656, et al., porphyrin derivatives and pyrazole derivatives (U.S. Patent No. 3,18,729, the same as No. 4,278,746, and JP-A-55-88064) Good. Ion luminescence will reduce the electricity. • Transit the country, the United States, the same as the 7 105, the same as the pyrazole, the newspaper, -93-200918640, 55-88065, the same as 49-105537, the same as the 55-51086 Japanese Patent Publication No. 56-80051, the same as No. 56-88141, the same as No. 57-45545, the same as No. 54-112637, the same as 55-7454 Reference No. 6 and the like), phenyldiamine derivative (U.S. Patent No. 3,615,404, Japanese Patent Publication No. 51-10105, the same as No. 46-3 7 1 2, and the same as 47-25 3 3 6 Japanese Laid-Open Patent Publication No. Hei-5-5-43-43, No. 54-110536, and No. 54-119925, etc., and arylamine derivatives (U.S. Patent No. 3,5 67,45 0) , the same as No. 3, 180, 703, the same as No. 3, 240, 597, the same as No. 3, 658, 520, the same as the fourth, 232, 1-3, the same as the 4, 175, 961, the same as the 4, 012, 376, special public 眧 49-35702 For reference, please refer to the Gazette, No. 39-27577, JP-A-55-144250, JP-A-56-119132, and 56-22437, and the West Patent No. 1, 1 1 0, 5 1 8 ), an amine-substituted Chalcone derivative (for reference to U.S. Patent No. 3,5,265, the disclosure of which is incorporated herein by reference), and a oxazole derivative (the disclosure of U.S. Patent No. 3,257, No. 2, No. 3, etc.) ), a styrene-based hydrazine derivative (for reference), and an anthrone derivative (Japanese Patent Laid-Open No. 5-6-4623) Japanese Patent Publication No. 5 4- 1 1 0 8 37, et al., 腙 derivative (U.S. Patent No. 3,717,462, JP-A-54-59143, and JP-A-55-52063, the same as 55-52064 No. 55-46760, the same as Japanese Patent Publication No. 55-85495, the same as Japanese Patent Publication No. 55-835350, the same as the Japanese Patent Publication No. 57-148749, and the Japanese Patent Publication No. Hei No. 2-311591, and the like, and stilbene Derivatives (JP-A-61-210363-94-200918640, the same as No. 61-228451, the same as No. 61-14642, the same as 6-722-5 5, the same as 62-47646, Japanese Patent Publication No. 62-3-6674, No. 62-10652, No. 62-30255, the same as Japanese Patent Publication No. 60-93455, the same as No. 60-94462, the same as No. 60-174749, the same as 6 0 - 1 7 5 No. 0, No. 2, No. 2, 295, 263, No. 2, No. 2, 295, 263, No. 2, No. 2, 920, 263 A conductive polymer oligomer (particularly a thiophene oligomer) disclosed in Japanese Laid-Open Patent Publication No. Hei No. Hei. Examples of the hole injecting material include a porphyrin compound (expressed by JP-A-63-295695, etc.), an aromatic tertiary amine compound, and a styrylamine compound (US Patent) Japanese Patent Publication No. 4,127,412, Japanese Patent Application Laid-Open No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. - 1 4425 0, the same as 56-; 1 191 32, the same as 61-295558, the same as 6 98353, the same as the 6 3 - 2 9 5 6 9 5, etc.) An aromatic tertiary amine compound is preferred. Further, in the case of having two condensed aromatic rings in the molecule described in U.S. Patent No. 5,061,569, for example, 4,4,-bis(N-(1-naphthyl)-N-anilino)biphenyl (hereinafter referred to as NPD), 4, 4, 4"-parameters (N-(3-) in which three triphenylamine units are linked in a starburst manner as described in JP-A-4-30086 Methylphenyl)-N-anilinotriphenylamine (hereinafter abbreviated as Μ TDATA), etc. -95- 200918640 Also, Patent Gazette No. 3 6 1 44〇5, 3 5 7 1 9 77 or US Patent The hexaazatribenzobenzene derivative described in 4,780,536 or the like can also be used as a hole injecting material. Further, an inorganic compound such as p-type Si or p-type SiC can also be used as a hole injecting material. The method of forming each layer of the light-emitting element is not particularly limited, and a conventionally known method of forming a vacuum vapor deposition method, a spin coating method, or the like can be used. The organic electroluminescence device of the present invention contains the above formula (1). The organic thin film layer of the compound may be a vacuum evaporation method, a molecular vapor deposition method (MBE method) or dissolved in a solvent. It is formed by a known method of a coating method such as a liquid immersion method, a spin coating method, a casting method, a bar coating method, or a roll coating method. The thickness of each organic layer of the organic electroluminescence device of the present invention is not particularly limited. When the general film thickness is too thin, defects such as pores may occur. On the contrary, when the thickness is too large, a voltage is applied and the efficiency is deteriorated, and it is usually in the range of several nm to 1 // m. [Examples] Next, the present invention will be described in more detail by way of examples and comparative examples, but the present invention is not limited by the contents of the examples, and the physical properties of the materials described in the following table are Their physical enthalpy is determined by the following: The triplet energy gap Eg (T) is determined by the luminescence spectrum. -96- 200918640 ie, 'each material is in EPA solvent (volume ratio diethyl ether: isopentane: Ethanol = 5 : 5 ·· 2 ) Dissolved from mol/L as a sample for calender measurement. The sample for calender measurement was placed in a quartz container, cooled to 7:7 Κ, irradiated with laser light, and irradiated with light. Determination by wavelength method. The connection line is drawn from the front side of the short-wavelength side of the luminescence spectrum, and the wavelength 値 at the intersection of the connection line and the bottom line is converted into energy, which is called the triple-term energy gap Eg ( Τ ). Moreover, the commercially available measuring device F-4 500 is used. (Measured by Hitachi).

-97-200918640 [Example 1] (Production of organic EL device) A glass substrate (manufactured by Asahi Glass Co., Ltd.) with an ITO transparent electrode of 2 5 mm X 7 5 mm X 0.7 mm thick was ultrasonically washed in isopropyl alcohol. After 5 minutes, clean the UV ozone for another 30 minutes. The cleaned glass substrate with the transparent electrode line was assembled on the substrate holder of the vacuum vapor deposition apparatus, and the surface of the transparent electrode line was first formed, and the film was formed to have a film thickness of 50 nm under the transparent electrode. The ΗΤ1 film functions as a hole injection transport layer. Further, the film formation of the hole injection transport layer is continued, and the novel host material compound F26 having a film thickness of 40 nm and Ir(ppy) 3 as a phosphorescent blend are heated by the resistor to 1% by mass. The film is formed into a co-evaporated film. This film can function as a light-emitting layer (a light-emitting layer). The formation of the light-emitting layer was continued, and a compound J having a film thickness of 1 〇 nm was formed, and the film was formed into ET1 having a film thickness of 40 nm. This film functions as an electron transport layer. Thereafter, L i F was used as an electron injecting electrode (cathode) to form a film thickness of 55 nm at a film forming speed of 0 to 1 nm/min. The metal A1' was deposited on the LiF layer to form a metal cathode to a film thickness of 150 nm to form an organic electroluminescence device. [Examples 2 to 4, Comparative Example 1] The novel main material compound F 2 6 of Example 1 was changed to the organic material in the same manner as in Example 1 except that the main material compound or blend shown in Table 1 below was used. Photoluminescent element. -98-200918640 [Evaluation of Luminescence Performance of Organic Electroluminescence Element] The organic EL elements produced in the above Examples 1 to 4 and Comparative Example 1 were driven to emit light by a direct current, and the current density was measured in a current density of 20 m A / cm 2 . Voltage, luminous efficiency and brightness half-life (initial brightness 10000 c d/m2). The results of these assessments are shown in Table 1. [Table 1] Main material blend voltage (V) Luminous efficiency (cd/A) Luminance half life Example 1 F26 Ir(ppy) 3 5.8 48.2 300 Example 2 F26 Ir(Ph-ppy) 3 5.7 53.4 2700 Example 3 F29 Ir(ppy)3 5.9 58.1 450 Example 4 F29 Ir(Ph-ppy)3 5.9 60.6 5000 Comparative Example 1 CBP Ir(ppy)3 5.7 53.1 30 As shown in Table 1, the main effect of the present invention is used for luminous efficiency. The organic electroluminescent elements of Examples 1 to 4 composed of the materials showed high external quantum efficiency and a particularly long lifetime. On the other hand, it is known that the life of Comparative Example 1 is short. The combination feature of the present invention is that the triplet energy gap of the main material and the triplet energy gap of the blend are suitable, so that the luminous efficiency can be improved, and the nitrogen-containing ring and the nitrogen atom in the main material are not replaced, so the luminescent material It has high resistance to holes and electrons, and thus it is possible to obtain a longer life than a combination known in the past. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a schematic block diagram showing an example of an organic electroluminescence device according to an embodiment of the present invention. [Explanation of main component symbols] 1 : Organic electroluminescent element 2 : Transparent substrate 3 : Anode 4 : Cathode 5 Chromium emitting layer 6 : Hole injection and transport layer 7 : Electron injection and transport layer 1 〇 : Organic thin film layer - 100 -

Claims (1)

200918640 X. Patent Application No. 1. An organic electroluminescent device characterized by having one or a plurality of organic thin film layers between a cathode and an anode, the organic thin film layer having at least one light emitting layer, the light emitting layer At least one of the main materials represented by the following formula (1) and at least one of the luminescent materials exhibiting luminescence; Ra*Arl-Ar2-Ar3-Rb (1) (in the formula (1), 'Ra, Rb, Ar1, Ar2 and Ar3 represent a benzene ring selected from a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted tribenzobenzene ring, and a substituted or unsubstituted phenanthrene ring. Ring; A r 2 is a substituted or unsubstituted benzene ring, or a substituted or unsubstituted 2,7 phenanthrene or tribenzo benzene ring, [Ra_Ari_] and [Rb_Ar3·] have mutually different structures. base). 2. The organic electroluminescent device according to claim 1, wherein in the formula (1), when 'Ra, Rb, Α γ 2 or Ar 3 has one or a plurality of substituents, the substituent is a carbon number of 6 ~22 aryl group 'carbon number i 2 〇 fct group, carbon number 1~2 卤 halogenated yard group, carbon number 5~i 8 cyclodecyl group, carbon number 3~20 methyl group, cyano group Or a halogen atom. 3. The organic electroluminescent device according to claim 2 or 2, wherein in the formula (1), Ar2 is a substituted or unsubstituted benzene ring, or a substituted or unsubstituted 2,7-phenanthrene In the case of a triphenyl benzene ring, Ari and Ar3 are mutually different aromatic hydrocarbon groups. 4. The organic electroluminescent device according to claim 1 or 2, wherein in the formula (1), 'Ar2 is a substituted or unsubstituted benzene ring, or -101 - 200918640 is substituted or unsubstituted 2 When a phenanthrenyl group or a tribenzophenone ring is used, Ar1 and Ar3 are mutually different condensed aromatic hydrocarbon groups. 5. The organic electroluminescent device according to claim 1 or 2, wherein at least one of 'Ra and Ar1 in the formula (1) is a substituted or unsubstituted naphthalene ring. 6. The organic electroluminescent device according to claim 1 or 2, wherein in the formula (1), Ra is a substituted or unsubstituted phenanthrene ring, and Ar1 is a substituted or unsubstituted benzene ring. 7. The organic electroluminescent device according to claim 1 or 2, wherein in the formula (1), 'Ra is a substituted or unsubstituted phenanthrene ring, and Ari is a substituted or unsubstituted naphthalene ring. 8. The organic electroluminescent device according to claim 1 or 2, wherein the main material has an excited triplet energy of 2.4 eV or more and 2.8 eV or less. The organic electroluminescent device of claim 1 or 2, wherein the photoluminescent material comprises a metal complex having a selected from the group consisting of Ir, Pt, Os, Au, Cu, Re, and The metal atom of RU and the ligand. 10. The organic electroluminescent device of claim 9, wherein the ligand has a primary metal bond. 1 1 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ the following. The organic electroluminescence-102-200918640 component of claim 1, wherein the organic thin film layer has an electron transport layer or an electron injection layer between the cathode and the light emitting layer, The electron transport layer or the electron injecting layer contains an aromatic ring having a nitrogen-containing 6-membered ring or a 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or a 5-membered ring skeleton. An organic electroluminescent device according to claim 1 or 2, wherein a reductive blend is added to an interface region between the cathode and the organic thin film layer. -103-